Understanding ketone hydrodeoxygenation for the production of fuels and feedstocks from biomass

Amanda E. King; Ty J. Brooks; Yong Hui Tian; Enrique R. Batista; Andrew D. Sutton

doi:10.1021/cs501965w

Understanding ketone hydrodeoxygenation for the production of fuels and feedstocks from biomass

Amanda E. King, Ty J. Brooks, Yong Hui Tian, Enrique R. Batista, Andrew D. Sutton

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H₂ (200 psi), and La(OTf)₃ in acetic acid to remove the oxygen atom at temperatures between 25 and 200 C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol. (Chemical Presented).

Original language	English
Pages (from-to)	1223-1226
Number of pages	4
Journal	ACS Catalysis
Volume	5
Issue number	2
DOIs	https://doi.org/10.1021/cs501965w
State	Published - Feb 6 2015
Externally published	Yes

Keywords

biomass
dehydration
hydrodeoxygenation
ketone reduction
mechanism

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10.1021/cs501965w

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abstract = "Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H2 (200 psi), and La(OTf)3 in acetic acid to remove the oxygen atom at temperatures between 25 and 200 C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol. (Chemical Presented).",

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AU - King, Amanda E.

AU - Brooks, Ty J.

AU - Tian, Yong Hui

AU - Batista, Enrique R.

AU - Sutton, Andrew D.

PY - 2015/2/6

Y1 - 2015/2/6

N2 - Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H2 (200 psi), and La(OTf)3 in acetic acid to remove the oxygen atom at temperatures between 25 and 200 C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol. (Chemical Presented).

AB - Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H2 (200 psi), and La(OTf)3 in acetic acid to remove the oxygen atom at temperatures between 25 and 200 C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol. (Chemical Presented).

KW - biomass

KW - dehydration

KW - hydrodeoxygenation

KW - ketone reduction

KW - mechanism

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Understanding ketone hydrodeoxygenation for the production of fuels and feedstocks from biomass

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